Chlorido(pentane-2,4-dionato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)copper(II)

Wong, Y.S.; Ng, C.H.; Ng, S.W.

doi:10.1107/S1600536809027111

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m934

doi:10.1107/S1600536809027111

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Chlorido(pentane-2,4-dionato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)copper(II)

Yew Sent Wong,^a Chew Hee Ng ^a and Seik Weng Ng ^b ^*

^aFaculty of Engineering and Science, Universiti Tunku Abdul Rahman, 53300 Kuala Lumpur, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 9 July 2009; accepted 10 July 2009; online 18 July 2009)

The Cu^II atom in the title compound, [Cu(C₅H₇O₂)Cl(C₁₂H₈N₂)], shows a distorted square-planar coordination; the chelating N and O atoms occupy the basal sites and the Cl atom the apical site. The square-pyramidal character along the Berry D_3h–C_4v pseudorotation pathway is 92%.

Related literature

For the synthesis and electronic spectrum, see: Kwik & Ang (1978 ). For isostructural CuBr(C₁₂H₈N₂)(C₅H₇O₂), see: Onawumi et al. (2008 ).

Experimental

Crystal data

[Cu(C₅H₇O₂)Cl(C₁₂H₈N₂)]
M_r = 378.30
Triclinic, $[P \overline 1]$
a = 7.5436 (1) Å
b = 9.0347 (2) Å
c = 11.9399 (2) Å
α = 85.638 (1)°
β = 72.329 (1)°
γ = 85.716 (1)°
V = 771.97 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.60 mm⁻¹
T = 163 K
0.35 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.605, T_max = 0.796
5384 measured reflections
3406 independent reflections
3151 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.073
S = 1.03
3406 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—Cl1	2.4717 (6)
Cu1—O1	1.927 (2)
Cu1—O2	1.936 (2)
Cu1—N1	2.038 (2)
Cu1—N2	2.025 (2)

O1—Cu1—O2	93.82 (7)
N1—Cu1—N2	81.04 (7)

Data collection: APEX2 (Bruker, 2008 ); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027111/xu2552sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027111/xu2552Isup2.hkl

checkCIF report

Related literature top

For the synthesis and electronic spectrum, see: Kwik & Ang (1978). For isostructural CuBr(C₁₂H₈N₂)(C₅H₇O₂), see: Onawumi et al. (2008).

Experimental top

Copper chloride dihydrate (0.17 g, 1 mmol) and 1,10-phenanthroline monohydrate (0.20 g, 1 mmol) were reacted in a 1:1 v/v methanol-water mixture (5 ml) to give a light green precipitate. The copper dichloride^.phenanthroline adduct (0.047 g, 0.15 mmol) was dissolved in a methanol-water mixture (5 ml) and this was treated with excess acetylacetone (5 ml) and 0.1 M sodium hydroxide (5 ml). The dark green solution was heated at 343 K for 30 min. Bluish-green crystals separated from the cool solution.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid (Barbour, 2001) plot of CuCl(C₁₂H₈N₂)(C₅H₇O₂) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radii.

Chlorido(pentane-2,4-dionato-κ²O,O')(1,10- phenanthroline-κ²N,N')copper(II) top

Crystal data top

[Cu(C₅H₇O₂)Cl(C₁₂H₈N₂)]	Z = 2
M_r = 378.30	F(000) = 386
Triclinic, P1	D_x = 1.627 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5436 (1) Å	Cell parameters from 4297 reflections
b = 9.0347 (2) Å	θ = 2.8–28.3°
c = 11.9399 (2) Å	µ = 1.60 mm⁻¹
α = 85.638 (1)°	T = 163 K
β = 72.329 (1)°	Block, blue
γ = 85.716 (1)°	0.35 × 0.35 × 0.15 mm
V = 771.97 (2) Å³

Data collection top

Bruker SMART APEX diffractometer	3406 independent reflections
Radiation source: fine-focus sealed tube	3151 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.605, T_max = 0.796	k = −11→11
5384 measured reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.073	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0226P)² + 1.0753P] where P = (F_o² + 2F_c²)/3
3406 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Cu(C₅H₇O₂)Cl(C₁₂H₈N₂)]	γ = 85.716 (1)°
M_r = 378.30	V = 771.97 (2) Å³
Triclinic, P1	Z = 2
a = 7.5436 (1) Å	Mo Kα radiation
b = 9.0347 (2) Å	µ = 1.60 mm⁻¹
c = 11.9399 (2) Å	T = 163 K
α = 85.638 (1)°	0.35 × 0.35 × 0.15 mm
β = 72.329 (1)°

Data collection top

Bruker SMART APEX diffractometer	3406 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3151 reflections with I > 2σ(I)
T_min = 0.605, T_max = 0.796	R_int = 0.015
5384 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.073	H-atom parameters constrained
S = 1.03	Δρ_max = 0.34 e Å⁻³
3406 reflections	Δρ_min = −0.43 e Å⁻³
210 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.74448 (4)	0.62243 (3)	0.25532 (2)	0.01986 (8)
Cl1	0.42757 (8)	0.74327 (6)	0.30310 (4)	0.02521 (12)
O1	0.7987 (2)	0.61537 (17)	0.40339 (13)	0.0275 (3)
O2	0.8805 (2)	0.79922 (17)	0.19426 (14)	0.0272 (3)
N1	0.7637 (2)	0.56785 (19)	0.08940 (15)	0.0197 (3)
N2	0.6667 (2)	0.41013 (19)	0.29186 (15)	0.0201 (3)
C1	0.8971 (4)	0.6884 (3)	0.5587 (2)	0.0391 (6)
H1A	0.7958	0.6294	0.6087	0.059*
H1B	0.8954	0.7830	0.5942	0.059*
H1C	1.0168	0.6335	0.5514	0.059*
C2	0.8716 (3)	0.7181 (3)	0.4385 (2)	0.0261 (5)
C3	0.9315 (3)	0.8491 (3)	0.3737 (2)	0.0313 (5)
H3	0.9691	0.9233	0.4126	0.038*
C4	0.9407 (3)	0.8800 (2)	0.2562 (2)	0.0256 (5)
C5	1.0312 (4)	1.0189 (3)	0.1944 (2)	0.0370 (6)
H5A	1.0362	1.0225	0.1113	0.056*
H5B	1.1580	1.0185	0.2005	0.056*
H5C	0.9584	1.1063	0.2314	0.056*
C6	0.8170 (3)	0.6495 (2)	−0.01113 (19)	0.0243 (4)
H6	0.8574	0.7464	−0.0101	0.029*
C7	0.8159 (3)	0.5982 (3)	−0.11824 (19)	0.0270 (5)
H7	0.8561	0.6597	−0.1884	0.032*
C8	0.7568 (3)	0.4593 (3)	−0.12245 (18)	0.0247 (4)
H8	0.7551	0.4239	−0.1950	0.030*
C9	0.6982 (3)	0.3695 (2)	−0.01631 (18)	0.0213 (4)
C10	0.6357 (3)	0.2224 (2)	−0.00981 (19)	0.0254 (4)
H10	0.6279	0.1814	−0.0790	0.030*
C11	0.5872 (3)	0.1408 (2)	0.0943 (2)	0.0263 (5)
H11	0.5476	0.0430	0.0966	0.032*
C12	0.5948 (3)	0.1995 (2)	0.20076 (18)	0.0216 (4)
C13	0.5500 (3)	0.1196 (2)	0.3117 (2)	0.0266 (5)
H13	0.5100	0.0210	0.3198	0.032*
C14	0.5653 (3)	0.1866 (2)	0.40724 (19)	0.0267 (5)
H14	0.5371	0.1341	0.4820	0.032*
C15	0.6226 (3)	0.3326 (2)	0.39506 (18)	0.0230 (4)
H15	0.6302	0.3778	0.4626	0.028*
C16	0.6529 (3)	0.3440 (2)	0.19648 (17)	0.0183 (4)
C17	0.7057 (3)	0.4300 (2)	0.08651 (17)	0.0183 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02849 (15)	0.01578 (13)	0.01782 (13)	−0.00745 (10)	−0.00941 (10)	−0.00008 (9)
Cl1	0.0299 (3)	0.0241 (3)	0.0245 (2)	−0.0016 (2)	−0.0116 (2)	−0.00471 (19)
O1	0.0404 (9)	0.0230 (8)	0.0251 (8)	−0.0066 (7)	−0.0179 (7)	−0.0008 (6)
O2	0.0357 (9)	0.0206 (8)	0.0261 (8)	−0.0129 (7)	−0.0080 (7)	−0.0005 (6)
N1	0.0240 (9)	0.0180 (8)	0.0181 (8)	−0.0041 (7)	−0.0076 (7)	0.0001 (6)
N2	0.0254 (9)	0.0168 (8)	0.0189 (8)	−0.0031 (7)	−0.0075 (7)	−0.0007 (6)
C1	0.0551 (17)	0.0374 (14)	0.0368 (13)	0.0050 (12)	−0.0312 (13)	−0.0112 (11)
C2	0.0282 (11)	0.0258 (11)	0.0291 (11)	0.0042 (9)	−0.0149 (9)	−0.0102 (9)
C3	0.0356 (13)	0.0265 (12)	0.0385 (13)	−0.0064 (10)	−0.0179 (11)	−0.0102 (10)
C4	0.0211 (10)	0.0200 (10)	0.0355 (12)	−0.0043 (8)	−0.0060 (9)	−0.0071 (9)
C5	0.0362 (13)	0.0262 (12)	0.0447 (14)	−0.0134 (10)	−0.0020 (11)	−0.0083 (10)
C6	0.0290 (11)	0.0211 (10)	0.0238 (10)	−0.0082 (8)	−0.0092 (9)	0.0032 (8)
C7	0.0327 (12)	0.0289 (12)	0.0200 (10)	−0.0064 (9)	−0.0093 (9)	0.0051 (8)
C8	0.0282 (11)	0.0293 (12)	0.0183 (9)	−0.0032 (9)	−0.0088 (8)	−0.0022 (8)
C9	0.0209 (10)	0.0231 (10)	0.0210 (10)	−0.0020 (8)	−0.0073 (8)	−0.0018 (8)
C10	0.0308 (11)	0.0237 (11)	0.0246 (10)	−0.0040 (9)	−0.0105 (9)	−0.0073 (8)
C11	0.0335 (12)	0.0188 (10)	0.0291 (11)	−0.0075 (9)	−0.0110 (9)	−0.0046 (8)
C12	0.0237 (10)	0.0187 (10)	0.0221 (10)	−0.0032 (8)	−0.0059 (8)	−0.0016 (8)
C13	0.0327 (12)	0.0179 (10)	0.0280 (11)	−0.0058 (9)	−0.0071 (9)	0.0017 (8)
C14	0.0350 (12)	0.0213 (11)	0.0230 (10)	−0.0057 (9)	−0.0078 (9)	0.0049 (8)
C15	0.0289 (11)	0.0218 (10)	0.0185 (9)	−0.0042 (8)	−0.0070 (8)	0.0004 (8)
C16	0.0190 (9)	0.0163 (9)	0.0196 (9)	−0.0013 (7)	−0.0058 (7)	−0.0011 (7)
C17	0.0184 (9)	0.0177 (9)	0.0195 (9)	−0.0022 (7)	−0.0065 (7)	−0.0010 (7)

Geometric parameters (Å, º) top

Cu1—Cl1	2.4717 (6)	C5—H5C	0.9800
Cu1—O1	1.927 (2)	C6—C7	1.396 (3)
Cu1—O2	1.936 (2)	C6—H6	0.9500
Cu1—N1	2.038 (2)	C7—C8	1.372 (3)
Cu1—N2	2.025 (2)	C7—H7	0.9500
O1—C2	1.271 (3)	C8—C9	1.420 (3)
O2—C4	1.273 (3)	C8—H8	0.9500
N1—C6	1.328 (3)	C9—C17	1.399 (3)
N1—C17	1.357 (3)	C9—C10	1.433 (3)
N2—C15	1.332 (3)	C10—C11	1.359 (3)
N2—C16	1.360 (3)	C10—H10	0.9500
C1—C2	1.507 (3)	C11—C12	1.431 (3)
C1—H1A	0.9800	C11—H11	0.9500
C1—H1B	0.9800	C12—C16	1.401 (3)
C1—H1C	0.9800	C12—C13	1.418 (3)
C2—C3	1.390 (3)	C13—C14	1.370 (3)
C3—C4	1.391 (3)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.402 (3)
C4—C5	1.506 (3)	C14—H14	0.9500
C5—H5A	0.9800	C15—H15	0.9500
C5—H5B	0.9800	C16—C17	1.435 (3)

O1—Cu1—O2	93.82 (7)	H5B—C5—H5C	109.5
O1—Cu1—N2	88.87 (7)	N1—C6—C7	122.4 (2)
O2—Cu1—N2	164.40 (7)	N1—C6—H6	118.8
O1—Cu1—N1	158.42 (7)	C7—C6—H6	118.8
O2—Cu1—N1	91.13 (7)	C8—C7—C6	120.18 (19)
N1—Cu1—N2	81.04 (7)	C8—C7—H7	119.9
O1—Cu1—Cl1	102.88 (5)	C6—C7—H7	119.9
O2—Cu1—Cl1	97.34 (5)	C7—C8—C9	118.7 (2)
N2—Cu1—Cl1	97.03 (5)	C7—C8—H8	120.6
N1—Cu1—Cl1	97.28 (5)	C9—C8—H8	120.6
C2—O1—Cu1	124.95 (14)	C17—C9—C10	119.20 (19)
C4—O2—Cu1	124.08 (15)	C17—C9—C8	116.96 (19)
C6—N1—C17	118.08 (18)	C10—C9—C8	123.8 (2)
C6—N1—Cu1	129.04 (15)	C11—C10—C9	120.7 (2)
C17—N1—Cu1	112.82 (13)	C11—C10—H10	119.7
C15—N2—C16	117.97 (18)	C9—C10—H10	119.7
C15—N2—Cu1	128.74 (15)	C10—C11—C12	121.3 (2)
C16—N2—Cu1	113.24 (13)	C10—C11—H11	119.4
C2—C1—H1A	109.5	C12—C11—H11	119.4
C2—C1—H1B	109.5	C16—C12—C13	116.90 (19)
H1A—C1—H1B	109.5	C16—C12—C11	118.84 (19)
C2—C1—H1C	109.5	C13—C12—C11	124.2 (2)
H1A—C1—H1C	109.5	C14—C13—C12	119.0 (2)
H1B—C1—H1C	109.5	C14—C13—H13	120.5
O1—C2—C3	125.0 (2)	C12—C13—H13	120.5
O1—C2—C1	115.3 (2)	C13—C14—C15	120.21 (19)
C3—C2—C1	119.7 (2)	C13—C14—H14	119.9
C2—C3—C4	125.1 (2)	C15—C14—H14	119.9
C2—C3—H3	117.4	N2—C15—C14	122.2 (2)
C4—C3—H3	117.4	N2—C15—H15	118.9
O2—C4—C3	125.5 (2)	C14—C15—H15	118.9
O2—C4—C5	116.0 (2)	N2—C16—C12	123.74 (18)
C3—C4—C5	118.4 (2)	N2—C16—C17	116.22 (18)
C4—C5—H5A	109.5	C12—C16—C17	120.03 (19)
C4—C5—H5B	109.5	N1—C17—C9	123.64 (18)
H5A—C5—H5B	109.5	N1—C17—C16	116.42 (18)
C4—C5—H5C	109.5	C9—C17—C16	119.93 (18)
H5A—C5—H5C	109.5

O2—Cu1—O1—C2	10.33 (19)	C6—C7—C8—C9	−0.3 (3)
N2—Cu1—O1—C2	174.95 (19)	C7—C8—C9—C17	−0.2 (3)
N1—Cu1—O1—C2	113.2 (2)	C7—C8—C9—C10	−179.3 (2)
Cl1—Cu1—O1—C2	−88.10 (18)	C17—C9—C10—C11	−1.2 (3)
O1—Cu1—O2—C4	−11.32 (19)	C8—C9—C10—C11	177.9 (2)
N2—Cu1—O2—C4	−110.9 (3)	C9—C10—C11—C12	0.8 (4)
N1—Cu1—O2—C4	−170.31 (18)	C10—C11—C12—C16	0.2 (3)
Cl1—Cu1—O2—C4	92.21 (18)	C10—C11—C12—C13	−178.6 (2)
O1—Cu1—N1—C6	−115.3 (2)	C16—C12—C13—C14	0.1 (3)
O2—Cu1—N1—C6	−12.0 (2)	C11—C12—C13—C14	178.9 (2)
N2—Cu1—N1—C6	−178.4 (2)	C12—C13—C14—C15	0.7 (3)
Cl1—Cu1—N1—C6	85.57 (19)	C16—N2—C15—C14	0.7 (3)
O1—Cu1—N1—C17	67.4 (2)	Cu1—N2—C15—C14	177.97 (16)
O2—Cu1—N1—C17	170.77 (15)	C13—C14—C15—N2	−1.1 (4)
N2—Cu1—N1—C17	4.33 (14)	C15—N2—C16—C12	0.1 (3)
Cl1—Cu1—N1—C17	−91.68 (14)	Cu1—N2—C16—C12	−177.56 (16)
O1—Cu1—N2—C15	17.41 (19)	C15—N2—C16—C17	−178.63 (19)
O2—Cu1—N2—C15	117.6 (3)	Cu1—N2—C16—C17	3.7 (2)
N1—Cu1—N2—C15	178.3 (2)	C13—C12—C16—N2	−0.5 (3)
Cl1—Cu1—N2—C15	−85.43 (19)	C11—C12—C16—N2	−179.4 (2)
O1—Cu1—N2—C16	−165.19 (15)	C13—C12—C16—C17	178.19 (19)
O2—Cu1—N2—C16	−65.0 (3)	C11—C12—C16—C17	−0.7 (3)
N1—Cu1—N2—C16	−4.33 (14)	C6—N1—C17—C9	−0.3 (3)
Cl1—Cu1—N2—C16	91.97 (14)	Cu1—N1—C17—C9	177.29 (16)
Cu1—O1—C2—C3	−3.0 (3)	C6—N1—C17—C16	178.75 (19)
Cu1—O1—C2—C1	178.82 (16)	Cu1—N1—C17—C16	−3.7 (2)
O1—C2—C3—C4	−7.9 (4)	C10—C9—C17—N1	179.7 (2)
C1—C2—C3—C4	170.2 (2)	C8—C9—C17—N1	0.5 (3)
Cu1—O2—C4—C3	5.2 (3)	C10—C9—C17—C16	0.7 (3)
Cu1—O2—C4—C5	−175.75 (16)	C8—C9—C17—C16	−178.49 (19)
C2—C3—C4—O2	6.6 (4)	N2—C16—C17—N1	0.0 (3)
C2—C3—C4—C5	−172.4 (2)	C12—C16—C17—N1	−178.79 (19)
C17—N1—C6—C7	−0.3 (3)	N2—C16—C17—C9	179.10 (19)
Cu1—N1—C6—C7	−177.38 (17)	C12—C16—C17—C9	0.3 (3)
N1—C6—C7—C8	0.6 (4)

Experimental details

Crystal data
Chemical formula	[Cu(C₅H₇O₂)Cl(C₁₂H₈N₂)]
M_r	378.30
Crystal system, space group	Triclinic, P1
Temperature (K)	163
a, b, c (Å)	7.5436 (1), 9.0347 (2), 11.9399 (2)
α, β, γ (°)	85.638 (1), 72.329 (1), 85.716 (1)
V (Å³)	771.97 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.60
Crystal size (mm)	0.35 × 0.35 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.605, 0.796
No. of measured, independent and observed [I > 2σ(I)] reflections	5384, 3406, 3151
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.03
No. of reflections	3406
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.43

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected geometric parameters (Å, º) top

Cu1—Cl1	2.4717 (6)	Cu1—N1	2.038 (2)
Cu1—O1	1.927 (2)	Cu1—N2	2.025 (2)
Cu1—O2	1.936 (2)

O1—Cu1—O2	93.82 (7)	N1—Cu1—N2	81.04 (7)

Acknowledgements

The authors thank MOSTI (grant No. 02-02-11-SF0033) and the University of Malaya for supporting this study.

References

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